How to Think Like an Entrepreneur and Why You Should Want to


My fascination with technology began when I realized it would help me become better at something I love—dealing with challenging problems. Originally, .orgSource was focused on software and hardware solutions. Today, although our scope has expanded to include integrating strategy, systems, and communications, problem-solving remains the core of our business.

The puzzle we will never complete is the most interesting. We are constantly seeking to understand how associations should position for success in an uncertain future. Four years ago, my business partner, Kevin Ordonez, and I began researching how Industry 4.0, would impact associations. We believed that technology such as blockchain, 3D printers, artificial intelligence, and other hallmarks of digital business, would have a significant impact; and we wanted to discover how savvy leaders were preparing for success in a volatile and highly competitive market.

We interviewed executives across the country about everything from digital transformation to remote work, change management, and cultural adaptation. Those conversations led to our book, “Association 4.0: Positioning for Success in an Era of Disruption.”

In the process of writing, we discovered something interesting. Although the associations represented professions from medicine to manufacturing, and their leaders were diverse in background and experience, patterns of behavior emerged that were familiar to us. The CEOs that welcomed change and were eager to experiment with new trends had a lot in common with the way Kevin and I see business.

Develop an Entrepreneurial Perspective

These executives were curious people. They weren’t afraid to take a calculated risk or to do an abrupt about-face when an initiative didn’t roll out as planned. In other words, they were acting like entrepreneurs. The more Kevin and I learned, the more convinced we became that the same approaches that helped us, and others, to grow a new business into a successful enterprise, are also strategies that association leaders can apply to navigate the uncertainty inherent in the digital marketplace.

To explore the entrepreneurial mindset more closely; we arranged to talk with some of our colleagues who have built companies that serve the association industry. Sharon Rice,  .orgSource’s Managing Director of Business Strategy explains why we thought their advice might be critical:

Business owners who start from scratch come through their own ranks.

“Helping diverse groups to develop winning strategies and translate vision into action is a significant focus of mine. One of the ironies of this work is that associations sometimes behave so differently than the industries they represent. While the marketplace thrives on the future, associations wear their history and tradition as a badge of honor. In a business world driven by invention, innovation, and profit, associations revolve around mission and service.

“That more passive approach worked well in a slower environment. But it doesn’t serve associations or their members when matched against a technological revolution that is delivering knockout punches. We can’t lay back on the ropes waiting for a break. It’s time for bolder strategies.

“Business owners who start from scratch come through their own ranks. One minute they’re the CEO describing their vision to a customer, the next they might be the receptionist fielding calls. It takes courage, ingenuity, and the willingness to learn and adapt to grow a business from the ground up. These are the same qualities that are needed to remain relevant when the idea of relevance is in constant flux.”

The conversations Kevin and I had were fascinating. We heard stories of adventure, disappointment, bravery, and reinvention. There was enough good advice to write a book, and that’s exactly what we did.  “Association 4.0: An Entrepreneurial Approach to Risk, Courage, and Transformation,” was the result of our research.
Although each individual brings a unique personality to the entrepreneurial spirit, these are some of the characteristics that we believe will be most beneficial for association leaders.

Welcome Risk and Change

You need the courage to take chances and the stomach to handle anxiety.

Every contributor to our book has an intimate relationship with risk. It’s a frenemy they’ve learned to manage. Sometimes that involves mitigating the downside. Other times it means taking a calculated leap of faith. Either way, there was universal agreement that growth and innovation are inextricably tied to risk. To thrive throughout the digital revolution, leaders must find ways to cross minefields like it’s a walk in the park. Sandy Marsico, Founder and CEO of Sandstorm Design, describes the challenge of balancing risk with growth like this:

“You need the courage to take chances and the stomach to handle anxiety. With a growing business, things change, but they don’t get easier. You have to believe in yourself,” Marsico advises. “You’re the one who drives success and encourages others to follow. You’re the leader, and you’re also the only one who can’t give up.

“I have a budget line for risk. These are not contingency dollars. These funds are designated for experimentation. I don’t always know how I’m going to spend the money, but when there is an opportunity, we are ready to seize it.”

Cultivate Innovation and Problem-Solving

A passion for innovation and problem solving was universal among our contributors. Building solutions is a way of life that, in some cases, began as early as childhood. We were surprised by the number of people who told us that their parents had also been business owners.

Whether they inherit a gene for invention or not, once they are thrown into the shark tank, entrepreneurs quickly learn to swim. They discover that survival means staying ahead of the competition by imagining the next problem before it surfaces; then, testing, experimenting, and iterating until an answer is found.

The concept of a minimum viable product was mentioned frequently. Smart innovators begin with a prototype, a product with just enough features to be attractive, allowing customer response to guide the final design. Instead of jumping to commitment; they wait for feedback to put a ring on it. This often means recalibrating to meet evolving conditions. Tracy King, Chief Learning Strategist of InspirED, always has her ear tuned to the market. She has learned to accept and grow from the verdict it hands down:“Allowing for learning through failure creates the freedom to solve problems instead of checking tasks off a list,” King explains. “We must ruthlessly sift through the challenges from the temporary distractions and seek the nuggets of truth in every successful disappointment. Incremental innovation is smart. So is listening deeply to the market and using MVPs to recalibrate. These are strategies that can help associations to see a real-time picture of their members’ needs.”

Understand Your Customers

While technology helps us to work more effectively. In the digital age, its role has moved beyond action and into the realm of understanding. Using data to develop a deep and empathetic perspective on members/customers is at the heart of digital transformation. Teri Carden, Co-Founder of 100Reviews, explains how her association clients use data to address member needs:

“We’ve seen several associations exporting data from their online communities and analyzing it with artificial intelligence tools to extract member sentiments and find fresh solutions to problems. Instead of playing a guessing game, they’re allowing the members to drive the conversation. Doing more listening can also generate ideas for products and services.”

Study Business and the Marketplace

There was general agreement that association CEOs should approach leadership from a business perspective and be knowledgeable about events and practices in the corporate world. Reading and networking widely were common habits of our contributors. Groups such as Vistagethe Entrepreneurs’ Organization, and .orgCommunity, our networking and professional development partner, are also resources for inspiration, advice, and studying market trends. Roy Chomko, CEO, Adage Technologies, credits a book with helping him run his business.

“A tool that’s made us more effective is using the Entrepreneur’s Operating System that was developed by Gino Wickman. Wickman’s book, “Traction: Get a Grip on Your Business,” and his other writings outline a simple process that entrepreneurs can follow to ensure that any organization is being run effectively.  Companies with between five and 250 employees are the target market for this system. I’ve often thought that the model could work effectively in an association environment.”

Accept the Challenge

While owning a business isn’t for everyone, any executive navigating the digital marketplace can benefit from operating more like a start-up. The courage to never stop being a pioneer, a student, and a risk-taker are basic skills for survival in a changing environment. Digital leaders need the humility to ask questions, to experiment, make mistakes, and start over. Finally, the future asks you to see beyond the present to potential.

The joy is in the challenge. Solving problems and finding answers that didn’t exist before is the essence of the entrepreneurial spirit. No one can execute all of this perfectly. But our contributors would tell you that perfection means the job is done, and an entrepreneur’s work is never finished. There is always a better idea or a new venture on the horizon.

Position Your Organization For Success

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